Fang-Lin Zhang1, Kai Hong1, Tuan-Jie Li1, Hojoon Park1, Jin-Quan Yu2. 1. The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA. 2. The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA. yu200@scripps.edu.
Abstract
Proximity-driven metalation has been extensively exploited to achieve reactivity and selectivity in carbon-hydrogen (C-H) bond activation. Despite the substantial improvement in developing more efficient and practical directing groups, their stoichiometric installation and removal limit efficiency and, often, applicability as well. Here we report the development of an amino acid reagent that reversibly reacts with aldehydes and ketones in situ via imine formation to serve as a transient directing group for activation of inert C-H bonds. Arylation of a wide range of aldehydes and ketones at the β or γ positions proceeds in the presence of a palladium catalyst and a catalytic amount of amino acid. The feasibility of achieving enantioselective C-H activation reactions using a chiral amino acid as the transient directing group is also demonstrated.
Proximity-driven metalation has been extensively exploited to achieve reactivity and selectivity inn class="Chemical">carbon-hydrogen (C-H) bond activation. Despite the substantial improvement in developing more efficient and practical directing groups, their stoichiometric installation and removal limit efficiency and, often, applicability as well. Here we report the development of an amino acid reagent that reversibly reacts with aldehydes and ketones in situ via imine formation to serve as a transient directing group for activation of inert C-H bonds. Arylation of a wide range of aldehydes and ketones at the β or γ positions proceeds in the presence of a palladium catalyst and a catalytic amount of amino acid. The feasibility of achieving enantioselective C-H activation reactions using a chiral amino acid as the transient directing group is also demonstrated.
Authors: Robin B Bedford; Simon J Coles; Michael B Hursthouse; Michael E Limmert Journal: Angew Chem Int Ed Engl Date: 2003-01-03 Impact factor: 15.336
Authors: Ru-Yi Zhu; Luo-Yan Liu; Han Seul Park; Kai Hong; Yongwei Wu; Chris H Senanayake; Jin-Quan Yu Journal: J Am Chem Soc Date: 2017-11-03 Impact factor: 15.419